Westchester County is alive with artistic expression this season. From community-driven galleries to seasonal fairs and historic estates hosting curated exhibitions, there's a refreshing sense of creativity everywhere you look. Whether you're an art lover, a curious traveler, or just looking for something new to explore near the Sleepy Hollow Hotel, this guide rounds up the best cultural stops to make while you're in town.
Peep Space is a contemporary gallery that regularly rotates exhibitions showcasing work by local and regional artists, and one of the best art galleries in Westchester County, NY. The space emphasizes thoughtful curation and provides a platform for emerging voices in the art world. Open on weekends, it’s a good stop for those looking to experience something a little more current and thought-provoking during their stay.
Getting There: Peep Space is a quick 7-minute drive or a manageable 25-minute walk. Parking is available nearby if you're driving.
On June 1st, Tarrytown’s Main Street will transform for the annual Tarrytown Street Fair from 10 a.m. to 4 p.m. This event brings together over 70 artists, craftspeople, performers, and local businesses for a full day of browsing, entertainment, and community connection. It’s a fun, relaxed way to enjoy art outside the traditional gallery setting, with plenty of food and music to go along with it.
Getting There: The street fair takes place on Main Street. You can get there in under 10 minutes with a rideshare.
Tarrytown and Sleepy Hollow are lined with independent shops and boutiques, many of which carry work by local artisans and designers. Highlights include ONA, a fair-trade gift shop offering handmade items from around the world, and Philipsburg Manor’s shop, which stocks locally made artwork and crafts. Pretty Funny Vintage offers clothing and folk art in a restored Victorian house. Bella’s Boutique features artisan jewelry and curated gifts, many made in the Hudson Valley. Rutheny Jewelry is a jewelry store that sells hand-sculpted pieces created by artist Jennifer Rutheny, who uses the long-lost art of wax casting in her intricate yet delicate designs.
Getting There: These shops are within a 1.5-mile radius of the hotel, making them easily walkable. You can also drive or use a taxi service if you’re planning to pick up a few things.
The gallery inside the visitor center at Rockefeller State Park Preserve is an underappreciated gem. It regularly features work by local artists that complements the serene beauty of the preserve itself. From May through June, stop by to see a floral-themed painting exhibition that celebrates spring in full color. While you're there, enjoy the park’s extensive carriage roads, perfect for a pre- or post-gallery stroll.
Getting There: The preserve is about a 10-minute drive from the hotel. Public transit is limited, so driving or ridesharing is the easiest option.
Bethany Arts Community in Ossining brings a wide mix of performances, workshops, and exhibitions to the region. From May 22 to September 11, you can explore works created through the Emerging Artist Residency—a program designed to spotlight fresh perspectives in visual arts, theater, dance, and writing. The campus itself is walkable, with indoor and outdoor installations.
Getting There: Bethany Arts Community is roughly a 15-minute drive from the hotel. Transit options are available, but a car or rideshare will get you there more directly.
KinoSaito in Verplanck offers gallery exhibitions, artist studios, and cultural programming all year long. On May 24, they’ll host a Members Only Opening Reception from 4 p.m. to 7 p.m., featuring new exhibitions. If you're interested in contemporary art with global influence, this is a perfect stop.
Getting There: Approximately 20 minutes by car from the hotel. Public transportation is limited, so plan to drive or use a rideshare service.
The Pelham Art Center offers rotating exhibitions, artist talks, and creative workshops for kids and adults. It’s a community-minded space where visitors can engage with artists and explore different forms of expression. Check their website for the current calendar of exhibitions and events.
Getting There: Located about 30 minutes away by car, Pelham Art Center is a good half-day trip from the Sleepy Hollow Hotel. Metro-North and local buses offer transit options, but driving is the most straightforward route.
The Harrison Public Library goes beyond books, hosting art exhibitions, author events, and other creative programming throughout the year. If you're interested in checking out local talent in a relaxed and welcoming setting, the library’s current exhibitions and community events are worth a look. Their 2025 Reading Challenge is also a great excuse to step inside and explore what’s on display.
Getting There: Roughly a 25-minute drive from the hotel. Public transportation is available, though routes may require transfers depending on your timing.
From sculpture and painting to jewelry and street fairs, there’s no shortage of ways to engage with Westchester’s creative community. These experiences offer more than just a look at local talent—they offer a chance to connect with the spirit of the area itself. Whether you’re planning to shop for handmade pieces, browse the buzzing art galleries in Westchester County, NY, or attend a live event, the Sleepy Hollow Hotel puts you close to all of it.
Book your stay at the Sleepy Hollow Hotel and enjoy easy access to the arts and culture of the Hudson Valley.